Triethylamine → HCID 53724108, compound

HRID 236511Notes

Reaction equation

HRID 236511 reaction equation
[C:1]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:20][C:21]([OH:23])=O)(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16].C(N(CC)CC)C.ClC(OCC)=O.[NH2:52][C@H:53]([C:57]([NH:59][C@H:60]([C:73]([O:75][CH2:76][C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=1)=[O:74])[CH2:61][CH2:62][C:63]([O:65][CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)=[O:64])=[O:58])[C@@H:54]([CH3:56])[OH:55]>O1CCCC1.C(OCC)(=O)C>[C:1]([O:18][CH:19]([CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[CH2:20][C:21]([NH:52][C@H:53]([C:57]([NH:59][C@H:60]([C:73]([O:75][CH2:76][C:77]1[CH:82]=[CH:81][CH:80]=[CH:79][CH:78]=1)=[O:74])[CH2:61][CH2:62][C:63]([O:65][CH2:66][C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1)=[O:64])=[O:58])[C@@H:54]([CH3:56])[OH:55])=[O:23])(=[O:17])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16]

Participants

7

Reactant 4

HCID 8471Triethylamine2×HCID 10928Ethyl chloroformateHCID 134890283-Hexadecanoyloxyoctadecanoic acidHCID 54173537HCID 54173537, compound

Product 1

HCID 53724108HCID 53724108, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 3-hexadecanoyloxyoctadecanoic acid (55 g) and triethylamine (16 ml) in tetrahydrofuran (500 ml) was added ethyl chloroformate (11 ml) dropwise with stirring at -20° C., and the mixture was stirred for 1 hour at the same temperature. To the mixture was added triethylamine (32 ml) and then, a solution of dibenzyl N-(L-threonyl)-L-glutamate (77 g) in tetrahydrofuran (100 ml) dropwise and the mixture was stirred for 3 hours at room temperature. Tetrahydrofuran was removed under reduced pressure to give the residue which was taken up in ethyl acetate. The ethyl acetate solution was washed with diluted hydrochloric acid and diluted sodium bicarbonate and dried. Evaporation of the solvent gave the residue which was recrystallized from ethanol to leave dibenzyl N-[N-(3-hexadecanoyloxyoctadecanoyl)-L-threonyl]-L-glutamate (79 g).

Workup

  1. stirringthe mixture was stirred for 1 hour at the same temperature
  2. customTetrahydrofuran was removed under reduced pressure
  3. customto give the residue which
  4. washThe ethyl acetate solution was washed with diluted hydrochloric acid and diluted sodium bicarbonate
  5. customdried
  6. customEvaporation of the solvent
  7. customgave the residue which
  8. customwas recrystallized from ethanol

Sources & evidence

ORD record
ord-6165d32b79f6434aa7c9acfe679dbac3
Source dataset
uspto-grants-1987_02
Patent number
US04643990

Reaction notes

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